Dyeing and printing of cellulose-containing textile material

ABSTRACT

A process for dyeing and printing cellulose-containing textile material, wherein the dye used is a compound of the general formula I &lt;IMAGE&gt;   where K is the radical of a coupling component of the pyridone, pyrazole or indole series, one of the radicals X, Y and Z is a carboxylic acid ester group of a total of 2 to 19 carbon atoms, a carboxamide group of a total of 1 to 19 carbon atoms, an unsubstituted or substituted sulfonic acid phenyl ester group or a sulfonamide group of a total of 6 to 18 carbon atoms, and the remaining substituents X, Y and Z are hydrogen, methyl, chlorine, bromine or nitro.

The present invention relates to a process for dyeing and printingcellulose-containing textile material, wherein the dye used is acompound of the general formula I ##STR2## where K is the radical of acoupling component of the pyridone, pyrazole or indole series,

one of the radicals X, Y and Z is a carboxylic acid ester group of atotal of 2 to 19 carbon atoms, a carboxamide group of a total of 1 to 19carbon atoms, an unsubstituted or substituted sulfonic acid phenyl estergroup or a sulfonamide group of a total of 6 to 18 carbon atoms, and

the remaining substituents X, Y and Z are hydrogen, methyl, chlorine,bromine or nitro.

The coupling component of the general formula KH preferably has theformula ##STR3## where R is hydrogen, C₁ -C₁₀ -alkyl, allyl, C₁ -C₄-alkyl which is substituted by C₁ -C₄ -alkoxy, by phenoxy, byphenoxyethoxy or by phenyl (which is itself unsubstituted orsubstituted), C₆ -C₁₂ -polyalkoxyalkyl, phenyl, cyclohexyl or norbornyl,

R¹ is phenyl which is unsubstituted or substituted by chlorine, bybromine, by C₁ -C₄ -alkyl or by C₁ -C₄ -alkoxy, or is methyl,

A is amino or hydroxyl,

B is methyl, a carboxylic acid ester group or unsubstituted orsubstituted carbamyl,

E is hydrogen, methyl, ethyl, β-cyanoethyl, β-carbamylethyl or allyl and

T is hydrogen, cyano, carbamyl or acetyl.

Examples of N-substituents of the carboxamide or sulfonamide groups ofthe diazo component are methyl, ethyl, propyl, butyl, n-hexyl, phenyl,benzyl, phenylethyl, 2-phenylpropyl, 2-ethylhexyl, 1,5-dimethylhexyl,n-octyl, n-dodecyl, n-tridecyl, 6-methylheptyl,3-(2-ethyl-hexoxy)-propyl, stearyl, cyclohexyl, β-methoxyethyl,β-butoxyethyl, γ-methoxypropyl, γ-butoxypropyl or γ-ethoxypropyl;furthermore, the N-substituted carboxamide or sulfonamide can be thepyrrolidide, piperidide or morpholide.

Examples of O-substituents of sulfonic acid ester groups are phenyl, o-,m- and p-tolyl, o-, m- and p-chlorophenyl and 2,5-dichlorophenyl.

Examples of suitable carboxylic acid ester groups are:

COOCH₃, COOC₂ H₅, COOC₃ H₇, COOC₄ H₉ -(n), COO--CH₂ --CH(CH₃)₂,COOC(CH₃)₃, COOC₄ H₈ Cl, COOC₅ H₁₁ (n), COOCH₂ C(CH₃)₃, ##STR4## COOC₁₂H₂₅, COOC₁₆ H₃₃, COOC₁₈ H₃₇, COOC₂ H₄ OC₂ H₅, COOC₂ H₄ OC₄ H₉, COOC₂ H₄OC₆ H₅, COOCH₂ C₆ H₅, COOC₂ H₄ C₆ H₅, ##STR5##

COOC₂ H₄ OC₆ H₅, COO(C₂ H₄ O)₂ CH₃, COO(C₂ H₄ O)₂ C₂ H₅, COO(C₂ H₄ O)₂C₄ H₉, COO(C₂ H₄ O)₃ C₂ H₅ and COO(C₂ H₄ O)₃ C₄ H₉.

The carbamyl and carboxylic acid ester groups listed as possiblesubstituents of the diazo component are also possible meanings of theradical B in the coupling component.

Specific examples of radicals R, in addition to those already mentioned,are:

CH₃, C₂ H₅, C₂ H₄ CN, C₃ H₇, C₄ H₉, CH₂ CH(CH₃)₂, C₆ H₁₃, ##STR6## C₂ H₄OCH₃, C₂ H₄ OC₄ H₉, C₃ H₆ OCH₃, C₃ H₆ OC₂ H₅, C₃ H₆ OC₃ H₇, C₃ H₆ OC₄H₉, C₃ H₆ OC₂ H₄ OC₆ H₅, ##STR7## C₃ H₆ OCH₂ C₆ H₅ and C₃ H₆ OC₂ H₄ C₆H₅.

The dyes of the general formula I, to be used according to theinvention, are obtained if an amine of the general formula III ##STR8##which is free from ionic groups is diazotized and coupled in aconventional manner with a component KH of the general formula II, X, Y,Z, R, R¹, A, B, E and T having the stated meanings.

Examples of suitable amines of the formula II are: the methyl, ethyl,n-butyl, i-butyl, n-hexyl, cyclohexyl, β-ethylhexyl, n-decyl, i-decyl,octadecyl, phenyl, 4'-tert.-butylphenyl, benzyl, phenylethyl,phenoxyethyl, β-ethoxy-ethyl, β-butoxy-ethyl, β-(β'-butoxy-ethoxy)-ethyland γ-(γ'-methoxy-propoxy)-propyl esters of 2-aminobenzoic acid and of4-aminobenzoic acid, and of the monohalo, dihalo, nitro and nitrohaloderivatives of these acids, eg. decyl 2-amino-3,5-dibromobenzoate,β-phenoxy-ethyl 2-amino-5-chloro-benzoate, decyl2-amino-5-nitro-benzoate and decyl 2-amino-3-bromo-5-nitro-benzoate, aswell as 2- and 4-aminobenzoic acid dimethylamide, diethylamide,iso-propylamide, di-n-butylamide, piperidide, morpholide, n-hexylamide,cyclohexylamide, ethylhexylamide, n- and i-decylamide, anilide,N-methylanilide, β-phenylethylamide andγ-(β'-phenoxy-ethoxy)-propylamide, as well as the corresponding amidesof the monohalo, dihalo, nitro and nitrohalo derivatives of the acids,eg. 2-amino-3,5-dibromobenzoic acid β-ethylhexylamide,2-amino-5-nitro-benzoic acid cyclohexylamide and2-amino-3-bromo-5-nitro-benzoic acid β-ethylhexylamide.

Further suitable amides are 4-aminobenzenesulfonic acid2-ethylhexyl-amide, tridecylamide, piperidide, β-phenylethyl-amide,2-phenylpropyl-amide, n- and i-octylamide, 6-methylhept-2-ylamide,n-hexylamide, γ-(β-phenoxyethoxy)-propylamide, n-dodecylamide,diisooctylamide, 2-ethylhexoxy-propylamide, octadecylamide, anilide,toluidide, N-methylanilide, N-ethylanilide, N-ethylcyclohexylamide,N-methylcyclohexylamide, cyclohexylamide, β-cyclohexylethylamide,benzylamide, di-n-butylamide and dibenzylamide, and the correspondingcompounds derived from 4-amino-3-chloro-, -3-bromo-, -3,5-dichloro- and-3,5-dibromo-benzenesulfonic acid; 4-aminobenzoic acid tridecylamide,2-phenylpropyl-amide, n- and i-octylamide, n-dodecylamide,diisooctylamide, 2-ethylhexoxy-propylamide, octadecylamide,N-ethylcyclohexylamide, N-methylcyclohexylamide, β-cyclohexylethyl-amideand benzylamide, and the corresponding amides of 4-amino-3-chloro-,-3-bromo-, -3,5-dichloro- and -3,5-dibromo-benzoic acid; phenyl, tolyl,chlorophenyl and 2,5-dichlorophenyl 2-aminobenzenesulfonate;2-aminobenzenesulfonic acid N-methylanilide, N-ethylanilide,N-methylcyclohexylamide, N-ethylcyclohexylamide, di-n-butylamide,dibenzylamide and di-(2-ethylhexyl)-amide, and the corresponding estersand amides of the monohalo, dihalo, nitro and nitrohalo derivatives of2-aminobenzenesulfonic acid, eg. 2-amino-5-nitro-benzenesulfonic acidN-ethylanilide, phenyl 2-amino-3,5-dibromobenzenesulfonate, phenyl2-amino-5-nitrobenzenesulfonate, phenyl2-amino-3-bromo-5-nitrobenzenesulfonate and2-amino-3,5-dibromobenzenesulfonic acid N-methylanilide; phenyl4-aminobenzenesulfonate, phenyl 4-amino-3,5-dibromobenzenesulfonate andtolyl 4-aminobenzenesulfonate; 4-amino-2,5-dichlorobenzenesulfonic acid2-ethylhexoxy-propylamide, 2-phenylethylamide,2-phenoxy-ethoxy-propylamide, n-octylamide and 2-ethylhexyl-amide.

Preferred dyes for use in the process according to the invention arethose of the formula ##STR9## where A, E, R, R¹ and T have the statedmeanings and R² is methyl or phenyl, and where one of X¹ and Y¹, one ofX² and Y², and one of X³ and Y³ is a carboxylic acid ester group orcarboxamide group of a total of 2 to 13 carbon atoms, or a sulfonamidegroup or unsubstituted or substituted sulfonic acid phenyl ester groupof a total of 6 to 18 carbon atoms, and of the remaining substituents,either X¹ or Y¹, and Z¹, are hydrogen, either X² or Y², and Z², arehydrogen, chlorine or bromine and either X³ or Y³, and Z³, are hydrogen,chlorine, bromine or nitro.

Suitable processes for applying the dyes of the formula I are, inparticular, those described in German Pat. No. 1,811,796, GermanLaid-Open Applications DOS No. 2,524,243 and DOS No. 2,528,743 andGerman patent application No. P 2,855,188.4. Details of the methods ofapplication may be found in the Examples, where parts and percentagesare by weight, unless stated otherwise.

EXAMPLE 1

A fabric comprising 65 parts of polyester fibers and 35 parts ofmercerized cotton is impregnated with a liquor which contains 80 g/l ofa 20% strength aqueous formulation of a water-insoluble yellow dispersedye of the formula ##STR10## and 80 g/l of a swelling agent and dyesolvent which in turn consists of 80 parts of a polyethylene glycol ofmolecular weight 1500 and 20 parts of a reaction product of 1 mole ofhexamethylenediamine with 15 moles of ethylene oxide. The pH of theliquor is brought to 6 with citric acid.

The impregnated fabric is dried for 60 seconds at 120° C. and is thenheated for 60 seconds at 215° C. to fix the dye. The fabric is thenrinsed cold and warm and is soaped for 20 minutes at 100° C. in thepresence of a commercial detergent.

A greenish yellow dyeing having good lightfastness, washfastness andfastness to crocking is obtained.

EXAMPLE 2

A polyester/cotton union fabric is printed with a formulation whichcomprises 10 parts of the dye from Example 1, 100 parts of a reactionproduct of polyethylene oxide, of molecular weight 300, with boric acidin the molar ratio of 3:1, 30 parts of oleic acid diethanolamide and 860parts of a 3% strength alginate thickener. The print is dried at 110° C.and is then treated for 5 minutes with live steam at 185° C., afterwhich the fabric is rinsed cold and soaped at 100° C., using acommercial detergent. A lightfast, washfast and solvent-fast greenishyellow print on a white ground is obtained.

EXAMPLE 3

A 65:35 polyester/cotton union fabric is printed with a paste whichcomprises 20 parts of the dye ##STR11## 110 parts of polyethylene oxideof molecular weight 350, 30 parts of oleic acid diethanolamide and 840parts of a 10% strength alginate thickener. The printed material isdried at 100° C. and the print is then fixed for 60 seconds with hot airat 190°-215° C. Thereafter, the print is rinsed cold and warm and soapedat 100° C., using a commercial detergent. A very greenish yellow print,with good fastness characteristics, is obtained on a white ground.

EXAMPLE 4

A fabric of 67 parts of polyester fibers and 33 parts of mercerizedcotton is impregnated with a liquor which contains 100 g/l of a mixtureof 80 parts of an ester of boric acid with polyethylene glycol(molecular weight about 800) in the molar ratio of 1:3 and 20 parts ofthe adduct of ethylenediamine and 35 moles of ethylene oxide. The wetpick-up is 80%. The fabric is then dried for 15 minutes at 60°-70° C.

The following print paste is printed onto the substrate:

500 parts of a 10% strength aqueous starch ether thickener

2 parts of citric acid

10 parts of sodium m-nitrobenzenesulfonate

50 parts of the dye ##STR12## and 438 parts of water.

The print is dried for 2 minutes at 130° C. and treated with hot air at210° C. for 90 seconds. After rinsing, a greenish yellow print on awhite ground is obtained.

EXAMPLE 5

A fabric of 65 parts of polyester fibers and 35 parts of mercerizedcotton is impregnated with a dye liquor which contains 20 g/l of a 20%strength formulation of the dye of the formula ##STR13## and, as aswelling agent and dye solvent, 60 g/l of a mixture of 1 part of areaction product of 1 mole of i-octylphenol with 14 moles of ethyleneoxide and 2 parts of a reaction product of 1 mole of piperazine with 16moles of ethylene oxide. The pH of the liquor is brought to 6 withglutaric acid. The fabric is dried for 60 seconds at 120° C. and the dyeis then fixed for 30 seconds at 225° C. The fabric is then rinsed coldand warm and washed at 100° C. in the presence of a commercialdetergent. A brilliant yellow dyeing having good washfastness andlightfastness is obtained.

EXAMPLE 6

A mercerized cotton twill is impregnated with an aqueous dye liquorwhich contains 80 g/l of the dye of the formula ##STR14## and 200 g of amixture of 80 parts of a polyethylene glycol of molecular weight 800 and20 parts of a block polymer of 1 mole of ethylenediamine, 8 moles ofpropylene oxide and 8 moles of ethylene oxide. The pH of the liquor isbrought to 6 with citric acid. The wet pick-up is 52%.

The fabric is then dried in a conventional manner at 120° C. and theprint is fixed for 30 seconds at 215° C. in a laboratory dryer. Afterrinsing and washing, an orange dyeing having good fastnesscharacteristics is obtained.

EXAMPLE 7

A cotton fabric is printed, by rotary screen printing, with aformulation which consists of 15 parts of the dye of the formula##STR15## 100 parts of polyethylene oxide of molecular weight 300 and885 parts of a 3% strength alginate thickener, and the print is dried at100° C. It is then treated with hot air at 200° C. for 1 minute, rinsedcold, soaped at the boil, again rinsed cold, and dried. A lightfast andwashfast yellow print on a white ground is obtained.

EXAMPLE 8

A 50:50 (by weight) polyester/cotton union fabric is impregnated with anaqueous liquor which contains 20 g/l of a 20% strength formulation ofthe dye of the formula ##STR16## and, as a swelling agent and dyesolvent, 50 g/l of a mixture of 80 parts of a polyethylene glycol ofmolecular weight 600 and 20 parts of a reaction product of 1 mole oftriethanolamine with 14 moles of ethylene oxide. The pH of the liquor isbrought to 7 with glutaric acid. The fabric is dried for 60 seconds at120° C. and then heated for 90 seconds at 210° C. It is then rinsed coldand warm and washed for 5 minutes at 100° C. in the presence of acommercial detergent. A lightfast and washfast golden yellow dyeing isobtained.

EXAMPLE 9

A 65:35 (by weight) polyester/cotton union fabric is printed with apaste which consists of 20 parts of the dye of the formula ##STR17## 120parts of a reaction product of polyethylene oxide, of molecular weight300, with boric acid in the molar ratio of 3:1 and 860 parts of a 10%strength alginate thickener. The print is dried at 105° C. and treatedwith live steam at 180° C. for 6 minutes. It is then rinsed with coldwater, soaped at 80° C., rinsed cold and dried. A lightfast and washfastgolden yellow print on a white ground is obtained.

Similarly, the dyes identified in the Table in terms of theirsubstituents give prints which have the hue shown and which as a rulepossess good fastness characteristics.

    __________________________________________________________________________     ##STR18##                                                                                                          Hue on polyester/                       Example                                                                            D                 T    R         cotton                                  __________________________________________________________________________    10                                                                                  ##STR19##        CN   C.sub.3 H.sub.7                                                                         greenish yellow                         11   "                 "    C.sub.2 H.sub.4 OCH.sub.3                                                               greenish yellow                         12   "                 "    C.sub.6 H.sub.13n                                                                       greenish yellow                         13   "                 "                                                                                   ##STR20##                                                                              greenish yellow                         14   "                 CONH.sub.2                                                                         CH.sub.3  greenish yellow                         15   "                 "    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         16   "                 "                                                                                   ##STR21##                                                                              greenish yellow                         17   "                 "    H         greenish yellow                         18                                                                                  ##STR22##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         19   "                 "    CH.sub.3  greenish yellow                         20   "                 "    C.sub.2 H.sub.4 OCH.sub.3                                                               greenish yellow                         21                                                                                  ##STR23##        "    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         22   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         23                                                                                  ##STR24##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         24   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         25   "                 CONH.sub.2                                                                         CH.sub.3  greenish yellow                         26   "                 COCH.sub.3                                                                         CH.sub.3  greenish yellow                         27                                                                                  ##STR25##        CN   H         greenish yellow                         28   "                 "    CH.sub.3  greenish yellow                         29   "                 CONH.sub.2                                                                         H         greenish yellow                         30   "                 CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         31   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      greenish yellow                         32   "                 COCH.sub.3                                                                         C.sub.4 H.sub. 9(n)                                                                     greenish yellow                         33                                                                                  ##STR26##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         34   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         35   "                 "                                                                                   ##STR27##                                                                              greenish yellow                         36   "                 "                                                                                   ##STR28##                                                                              greenish yellow                         37   "                 COCH.sub.3                                                                         CH.sub.3  greenish yellow                         38                                                                                  ##STR29##        CN   H         greenish yellow                         39   "                 "    CH.sub.3  greenish yellow                         40   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      greenish yellow                         41                                                                                  ##STR30##        CN   CH.sub.3  greenish yellow                         42   "                 "    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         43   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         44   "                 "    C.sub.2 H.sub.4 OCH.sub.3                                                               greenish yellow                         45                                                                                  ##STR31##        "    H         yellow                                  46   "                 "    CH.sub.3  yellow                                  47   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  48   "                 COCH.sub.3                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  49                                                                                  ##STR32##        CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  50   "                 COCH.sub.3                                                                         CH.sub.3  yellow                                  51                                                                                  ##STR33##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         52                                                                                  ##STR34##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         53                                                                                  ##STR35##        CN   C.sub.4 H.sub.9(n)                                                                      greenish yellow                         54   "                 "                                                                                   ##STR36##                                                                              greenish yellow                         55   "                 "                                                                                   ##STR37##                                                                              greenish yellow                         56   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         57                                                                                  ##STR38##        "                                                                                   ##STR39##                                                                              greenish yellow                         58   "                 "    C.sub.6 H.sub.13(n)                                                                     greenish yellow                         59                                                                                  ##STR40##        "    CH.sub.3  yellow                                  60   "                 "    C.sub.4 H.sub.9(n)                                                                      yellow                                  61   "                 "    C.sub.6 H.sub.13(n)                                                                     yellow                                  62   "                 "                                                                                   ##STR41##                                                                              yellow                                  63   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  64                                                                                  ##STR42##        CN   C.sub.4 H.sub.9(n)                                                                      yellow                                  65   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  66   "                 CN   CH.sub.3  yellow                                  67   "                 CONH.sub.2                                                                         CH.sub.3  yellow                                  68                                                                                  ##STR43##        CN   CH.sub.2 CHCH.sub.2                                                                     yellow                                  69                                                                                  ##STR44##        "    CH.sub.2 CHCH.sub.2                                                                     yellow                                  70   "                 "    C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                         yellow                                  71                                                                                  ##STR45##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  72                                                                                  ##STR46##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  73   "                 H    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         74                                                                                  ##STR47##        CN   C.sub.4 H.sub.9(n)                                                                      yellow                                  75   "                 CONH.sub.2                                                                         C.sub.4 H.sub.9(n)                                                                      yellow                                  76   "                 CN   CH.sub.3  yellow                                  77                                                                                  ##STR48##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  78                                                                                  ##STR49##        CONH.sub.2                                                                         CH.sub.3  yellow                                  79   "                 CN   CH.sub.3  yellow                                  80                                                                                  ##STR50##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  81                                                                                  ##STR51##        "                                                                                   ##STR52##                                                                              yellow                                  82   "                 "    C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                         yellow                                  83                                                                                  ##STR53##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  84   "                 H    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         85                                                                                  ##STR54##        CN                                                                                  ##STR55##                                                                              yellow                                  86   "                 "    C.sub.6 H.sub.13(n)                                                                     yellow                                  87                                                                                  ##STR56##        "                                                                                   ##STR57##                                                                              yellow                                  88                                                                                  ##STR58##        "    C.sub.4 H.sub.9(n)                                                                      yellow                                  89   "                 H    C.sub.4 H.sub.9(n)                                                                      greenish yellow                         90                                                                                  ##STR59##        CN   CH.sub.3  yellow                                  91   "                 CONH.sub.2                                                                         CH.sub.3  yellow                                  92                                                                                  ##STR60##        COCH.sub.3                                                                         CH.sub.3  yellow                                  93   "                 CN   C.sub.2 H.sub.5                                                                         yellow                                  94   "                 H    C.sub.4 H.sub.9                                                                         greenish yellow                         95                                                                                  ##STR61##        CN   CH.sub.3  yellow                                  96   "                 "    C.sub.4 H.sub.9(n)                                                                      yellow                                  97                                                                                  ##STR62##        "    CH.sub.3  yellow                                  __________________________________________________________________________

    ______________________________________                                         ##STR63##                                                                                                     Hue on poly-                                 Ex.  D                R          ester/cotton                                 ______________________________________                                         98                                                                                 ##STR64##       C.sub.4 H.sub.9(n)                                                                       greenish yellow                               99  "                CH.sub.3   "                                            100  "                                                                                               ##STR65## "                                            101  "                C.sub.6 H.sub.13(n)                                                                      "                                            102                                                                                 ##STR66##       C.sub.4 H.sub.9(n)                                                                       "                                            103  "                CH.sub.3   "                                            104  "                C.sub.3 H.sub.6OCH.sub.3                                                                 "                                            105                                                                                 ##STR67##       C.sub.6 H.sub.13(n)                                                                      "                                            106  "                                                                                               ##STR68## "                                            107                                                                                 ##STR69##       C.sub. 3 H.sub.6 OCH.sub.3                                                               "                                            ______________________________________                                    

    __________________________________________________________________________     ##STR70##                                                                                                        Hue on polyester/                         Example                                                                            D                  A  R.sub.1  cotton                                    __________________________________________________________________________    108                                                                                 ##STR71##         NH.sub.2                                                                          ##STR72##                                                                             yellow                                    109  "                  "                                                                                 ##STR73##                                                                             yellow                                    110  "                  "                                                                                 ##STR74##                                                                             yellow                                    111  "                  "                                                                                 ##STR75##                                                                             yellow                                    112                                                                                 ##STR76##         OH                                                                                ##STR77##                                                                             yellow                                    113  "                  "                                                                                 ##STR78##                                                                             yellow                                    114  "                  "                                                                                 ##STR79##                                                                             yellow                                    115  "                  "                                                                                 ##STR80##                                                                             yellow                                    116                                                                                 ##STR81##         "                                                                                 ##STR82##                                                                             yellow                                    117  "                  H.sub.2 N                                                                         ##STR83##                                                                             yellow                                    118                                                                                 ##STR84##         NH.sub.2                                                                          ##STR85##                                                                             yellow                                    119  "                  "                                                                                 ##STR86##                                                                             yellow                                    120  "                  OH                                                                                ##STR87##                                                                             yellow                                    121  "                  "                                                                                 ##STR88##                                                                             yellow                                    122  "                  "                                                                                 ##STR89##                                                                             yellow                                    123                                                                                 ##STR90##         "                                                                                 ##STR91##                                                                             yellow                                    124  "                  "                                                                                 ##STR92##                                                                             yellow                                    125  "                  "                                                                                 ##STR93##                                                                             yellow                                    126                                                                                 ##STR94##         H.sub.2 N                                                                         ##STR95##                                                                             yellow                                    127                                                                                 ##STR96##         OH "        yellow                                    128                                                                                 ##STR97##         H.sub.2 N                                                                        "        yellow                                    129                                                                                 ##STR98##         OH "        golden yellow                             130  "                  "                                                                                 ##STR99##                                                                             yellow                                    131                                                                                 ##STR100##        "                                                                                 ##STR101##                                                                            yellow                                    132  "                  "                                                                                 ##STR102##                                                                            yellow                                    133                                                                                 ##STR103##        "  "        yellow                                    134                                                                                 ##STR104##        "  "        yellow                                    135                                                                                 ##STR105##        "  "        yellow                                    136                                                                                 ##STR106##        NH.sub.2                                                                          ##STR107##                                                                            yellow                                    137                                                                                 ##STR108##        "  C.sub.6 H.sub.5                                                                        yellow                                    138                                                                                 ##STR109##        OH "        yellow                                    139                                                                                 ##STR110##        NH.sub.2                                                                         "        golden yellow                             140                                                                                 ##STR111##        OH "        yellow                                    141                                                                                 ##STR112##        NH.sub.2                                                                         "        golden yellow                             142                                                                                 ##STR113##        OH "        yellow                                    143                                                                                 ##STR114##        NH.sub.2                                                                         "        yellow                                    144                                                                                 ##STR115##        "  "        yellow                                    145  "                  "                                                                                 ##STR116##                                                                            yellow                                    146  "                  OH "        yellow                                    147  "                  "                                                                                 ##STR117##                                                                            yellow                                    148                                                                                 ##STR118##        "  C.sub.6 H.sub.5                                                                        yellow                                    149                                                                                 ##STR119##        "  "        yellow                                    150  "                  "                                                                                 ##STR120##                                                                            yellow                                    151                                                                                 ##STR121##        "  "        yellow                                    152  "                  "  C.sub.6 H.sub.5                                                                        yellow                                    153                                                                                 ##STR122##        "  "        yellow                                    154                                                                                 ##STR123##        "  "        yellow                                    __________________________________________________________________________

    __________________________________________________________________________     ##STR124##                                                                                                       Hue on polyester/                         Example                                                                            D                  C      R.sub.1                                                                            cotton                                    __________________________________________________________________________    155                                                                                 ##STR125##        H                                                                                     ##STR126##                                                                        brownish yellow                           156  "                  CH.sub.3                                                                             "    golden yellow                             157                                                                                 ##STR127##        H      "    orange                                    158                                                                                 ##STR128##        CH.sub.3                                                                             "    golden yellow                             159                                                                                 ##STR129##        H      "    yellowish brown                           160  "                  CH.sub.3                                                                             "    yellowish brown                           161                                                                                 ##STR130##        H      "    yellowish brown                           162  "                  CH.sub.3                                                                             "    yellowish brown                           163                                                                                 ##STR131##        H      "    yellowish brown                           164  "                  CH.sub.3                                                                             "    yellowish brown                           165                                                                                 ##STR132##        H      "    yellowish brown                           166  "                  CH.sub.3                                                                             "    yellowish brown                           167                                                                                 ##STR133##        "      "    yellowish brown                           168  "                  C.sub.2 H.sub.4 CN                                                                   "    yellowish brown                           169                                                                                 ##STR134##        "      "    yellowish brown                           170                                                                                 ##STR135##        C.sub.2 H.sub.4 CONH.sub.2                                                           "    yellowish brown                           171                                                                                 ##STR136##        H      "    yellowish brown                           172  "                  CH.sub.3                                                                             "    yellowish brown                           173                                                                                 ##STR137##        "      C.sub.6 H.sub.5                                                                    golden yellow                             174                                                                                 ##STR138##        "      "    golden yellow                             175                                                                                 ##STR139##        "      "    golden yellow                             176                                                                                 ##STR140##        "      "    golden yellow                             __________________________________________________________________________

    __________________________________________________________________________     ##STR141##                                                                   Example                                                                            D            T    R                                                      __________________________________________________________________________    177                                                                                 ##STR142##  CN   C.sub.10 H.sub.21(n)                                                                      greenish yellow                            178  "            "    C.sub.12 H.sub.25                                                                         "                                          179                                                                                 ##STR143##  "     "          "                                          180  "            CONH.sub.2                                                                          "          "                                                                 C.sub.9 H.sub.19                                       181  "            CN   C.sub.10 H.sub.21                                                                      1:1:1                                                                            "                                                                 C.sub.11 H.sub.23                                      __________________________________________________________________________

We claim:
 1. A process for dyeing and printing water-swellablecellulosic materials and blends thereof with synthetic materials in thepresence of water and a solvent that is capable of maintaining cellulosein the swollen state, wherein the dye used is a compound of the generalformula: ##STR144## wherein B is an alkyl group containing from 8 to 18carbon atoms,R is hydrogen or an alkyl group containing from 3 to 7carbon atoms, and T is hydrogen, cyano, carbamyl or acetyl.
 2. Theprocess of claim 1 wherein B contains 10 carbon atoms, R contains 4carbon atoms and T is cyano.
 3. The process of claim 1 wherein Bcontains 10 carbon atoms, R contains 4 carbon atoms and T is carbamyl.4. The process of claim 1 wherein B contains 18 carbon atoms, R ishydrogen and T is cyano.
 5. The process of claim 1 wherein B contains 18carbon atoms, R contains 4 carbon atoms and T is cyano.
 6. The processof claim 1 wherein B contains 10 carbon atoms, R contains 6 carbon atomsand T is cyano.
 7. The process of claim 1 wherein B contains 18 carbonatoms, R contains 6 carbon atoms and T is cyano.